#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006303.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2006303
loop_
_publ_author_name
'Lalancette, R. A.'
'Thompson, H. W.'
'Cot\'e, M. L.'
_publ_section_title
;
 Hydrogen-Bonding Pattern of an \a,\b-Unsaturated \d-Keto Acid:
 1',3'-Dihydro-2-methyl-6-oxospiro[2-cyclohexene-1,2'-2'<i>H</i>-indene]-3-carboxylic
 Acid
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              901
_journal_page_last               903
_journal_volume                  53
_journal_year                    1997
_chemical_formula_analytical     'C16 H16 O3'
_chemical_formula_moiety         'C16 H16 O3'
_chemical_formula_structural     'C16 H16 O3'
_chemical_formula_sum            'C16 H16 O3'
_chemical_formula_weight         256.29
_chemical_melting_point          469
_chemical_name_systematic
Spiro[3-carboxy-1',3'-dihydro-2-methyl-6-oxo-2-cyclohexene-1,2'-[2H]indene]
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90
_cell_angle_beta                 90.669(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.515(3)
_cell_length_b                   5.8352(9)
_cell_length_c                   22.854(3)
_cell_measurement_reflns_used    19
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      12.4
_cell_measurement_theta_min      7.0
_cell_volume                     2602.3(7)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1991)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1994)'
_diffrn_ambient_temperature      295(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       2\q/\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0725
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            3020
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         1.50
_diffrn_standards_decay_%        2.50
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   'Face-indexed numerical'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      1.300(10)
_exptl_crystal_density_method    'flotation in cyclohexane/CCl~3~Br'
_exptl_crystal_description       Rhombus
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.193
_refine_ls_extinction_coef       0.0133(15)
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 1994)'
_refine_ls_goodness_of_fit_all   0.904
_refine_ls_goodness_of_fit_obs   1.069
_refine_ls_hydrogen_treatment    'H atoms: see below'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.904
_refine_ls_restrained_S_obs      1.069
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_obs          0.0555
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0845P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1480
_refine_ls_wR_factor_obs         0.1328
_reflns_number_observed          1376
_reflns_number_total             2276
_reflns_observed_criterion       >4sigma(F)
_[local]_cod_data_source_file    fg1273.cif
_[local]_cod_data_source_block   lalancette
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (6
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (9
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (8 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2006303
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.091(2) 0.0571(13) 0.0744(14) 0.0358(12) -0.0118(12) -0.0088(11)
O2 0.0678(14) 0.126(2) 0.095(2) 0.0455(15) -0.0239(12) -0.062(2)
O3 0.087(2) 0.141(2) 0.116(2) 0.056(2) -0.0347(15) -0.093(2)
C1 0.0507(14) 0.0320(13) 0.0365(12) 0.0021(12) 0.0022(10) -0.0028(11)
C2 0.0457(14) 0.0298(13) 0.0382(12) 0.0018(11) 0.0005(11) 0.0010(10)
C3 0.0475(14) 0.0387(14) 0.0412(13) 0.0107(12) -0.0010(11) -0.0036(11)
C4 0.061(2) 0.060(2) 0.0475(15) 0.0209(15) -0.0129(13) -0.0126(13)
C5 0.052(2) 0.058(2) 0.055(2) 0.0121(14) -0.0139(13) -0.0092(14)
C6 0.0533(15) 0.045(2) 0.0429(14) 0.0135(13) 0.0045(11) -0.0026(12)
C7 0.054(2) 0.053(2) 0.0434(14) 0.0142(14) -0.0065(12) -0.0118(13)
C8 0.0508(15) 0.054(2) 0.0501(15) 0.0048(13) -0.0077(13) -0.0080(13)
C1' 0.064(2) 0.0328(13) 0.0441(14) -0.0003(13) 0.0052(12) -0.0037(11)
C3' 0.057(2) 0.0379(14) 0.0439(14) -0.0016(13) 0.0063(12) -0.0033(12)
C3A' 0.0440(13) 0.0371(14) 0.0393(13) 0.0065(12) 0.0040(10) -0.0020(11)
C4' 0.051(2) 0.061(2) 0.0466(15) 0.0052(14) 0.0077(12) 0.0043(13)
C5' 0.057(2) 0.088(2) 0.0386(15) 0.015(2) 0.0021(13) 0.001(2)
C6' 0.064(2) 0.074(2) 0.047(2) 0.003(2) -0.0084(14) -0.016(2)
C7' 0.059(2) 0.050(2) 0.051(2) -0.0010(14) -0.0054(13) -0.0088(13)
C7A' 0.0505(14) 0.0379(14) 0.0387(13) 0.0043(12) 0.0017(11) -0.0043(11)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 0.22623(11) 0.0834(4) 0.40749(9) 0.0742(7) Uani d . 1 O
O2 -0.00387(11) 0.7839(5) 0.45066(10) 0.0964(9) Uani d . 1 O
O3 0.08056(13) 0.8900(5) 0.50604(12) 0.1148(12) Uani d . 1 O
H3C 0.0524(18) 1.001(6) 0.5267(15) 0.100 Uiso d . 1 H
C1 0.14505(12) 0.3346(4) 0.36083(9) 0.0397(6) Uani d . 1 C
C2 0.09264(12) 0.4961(4) 0.38794(9) 0.0379(6) Uani d . 1 C
C3 0.10373(12) 0.5953(4) 0.44036(10) 0.0425(6) Uani d . 1 C
C4 0.16771(10) 0.5539(3) 0.47702(8) 0.0561(8) Uani d . 1 C
C5 0.22660(10) 0.4681(3) 0.44036(8) 0.0549(7) Uani d R 1 C
C6 0.20233(13) 0.2738(5) 0.40381(10) 0.0470(7) Uani d . 1 C
C7 0.05641(14) 0.7634(5) 0.46599(11) 0.0504(7) Uani d . 1 C
C8 0.03080(13) 0.5416(5) 0.34970(11) 0.0516(7) Uani d . 1 C
C1' 0.11139(14) 0.1173(4) 0.33412(10) 0.0471(7) Uani d . 1 C
C3' 0.18024(13) 0.4602(4) 0.30772(10) 0.0462(7) Uani d . 1 C
C3A' 0.15637(12) 0.3313(4) 0.25443(10) 0.0401(6) Uani d . 1 C
C4' 0.16860(13) 0.3876(5) 0.19631(11) 0.0531(7) Uani d . 1 C
C5' 0.14300(14) 0.2446(6) 0.15315(11) 0.0612(9) Uani d . 1 C
C6' 0.10716(15) 0.0488(6) 0.16738(12) 0.0616(8) Uani d . 1 C
C7' 0.09513(14) -0.0052(5) 0.22518(11) 0.0535(7) Uani d . 1 C
C7A' 0.11947(12) 0.1384(4) 0.26884(10) 0.0424(6) Uani d . 1 C
H4A 0.18050(10) 0.6923(3) 0.49707(8) 0.063(3) Uiso d R 1 H
H4B 0.15730(10) 0.4399(3) 0.50587(8) 0.063(3) Uiso d R 1 H
H5A 0.24263(10) 0.5903(3) 0.41596(8) 0.063(3) Uiso d R 1 H
H5B 0.26387(10) 0.4176(3) 0.46495(8) 0.063(3) Uiso d R 1 H
H8A 0.0408(5) 0.500(4) 0.3101(2) 0.058(7) Uiso calc PR 0.76(3) H
H8B 0.0194(8) 0.7015(9) 0.3514(9) 0.058(7) Uiso calc PR 0.76(3) H
H8C -0.0072(4) 0.452(3) 0.3632(7) 0.058(7) Uiso calc PR 0.76(3) H
H8D -0.0055(4) 0.603(4) 0.3731(2) 0.058(7) Uiso calc PR 0.24(3) H
H8E 0.0160(8) 0.4011(9) 0.3317(9) 0.058(7) Uiso calc PR 0.24(3) H
H8F 0.0425(4) 0.650(3) 0.3199(7) 0.058(7) Uiso calc PR 0.24(3) H
H1'A 0.06372(14) 0.1111(4) 0.34392(10) 0.063(3) Uiso d R 1 H
H1'B 0.13496(14) -0.0167(4) 0.34812(10) 0.063(3) Uiso d R 1 H
H3'A 0.22923(13) 0.4522(4) 0.31145(10) 0.063(3) Uiso d R 1 H
H3'B 0.16662(13) 0.6181(4) 0.30565(10) 0.063(3) Uiso d R 1 H
H4' 0.19437(13) 0.5220(5) 0.18645(11) 0.066(4) Uiso d R 1 H
H5' 0.14998(14) 0.2821(6) 0.11275(11) 0.066(4) Uiso d R 1 H
H6' 0.09058(15) -0.0491(6) 0.13656(12) 0.066(4) Uiso d R 1 H
H7' 0.07072(14) -0.1422(5) 0.23525(11) 0.066(4) Uiso d R 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C7 O3 H3C 122(2) y
C6 C1 C2 111.9(2) ?
C6 C1 C1' 111.6(2) ?
C2 C1 C1' 112.4(2) ?
C6 C1 C3' 106.3(2) ?
C2 C1 C3' 108.9(2) ?
C1' C1 C3' 105.2(2) ?
C3 C2 C8 124.1(2) ?
C3 C2 C1 121.7(2) ?
C8 C2 C1 114.2(2) ?
C2 C3 C7 123.0(2) y
C2 C3 C4 123.1(2) ?
C7 C3 C4 113.7(2) y
C3 C4 C5 111.86(11) ?
C6 C5 C4 108.96(12) ?
O1 C6 C5 122.9(2) y
O1 C6 C1 122.7(2) y
C5 C6 C1 114.4(2) y
O2 C7 O3 119.8(2) y
O2 C7 C3 123.6(2) y
O3 C7 C3 116.6(2) y
C7A' C1' C1 105.9(2) ?
C3A' C3' C1 104.9(2) ?
C7A' C3A' C4' 121.1(2) ?
C7A' C3A' C3' 111.9(2) ?
C4' C3A' C3' 127.0(2) ?
C5' C4' C3A' 118.3(3) ?
C6' C5' C4' 120.8(2) ?
C5' C6' C7' 120.4(3) ?
C6' C7' C7A' 119.4(3) ?
C3A' C7A' C7' 119.9(2) ?
C3A' C7A' C1' 111.4(2) ?
C7' C7A' C1' 128.7(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C6 1.207(3) y
O2 C7 1.229(3) y
O3 C7 1.263(3) y
C1 C6 1.522(3) y
C1 C2 1.527(3) ?
C1 C1' 1.550(3) ?
C1 C3' 1.581(3) ?
C2 C3 1.346(3) ?
C2 C8 1.505(3) ?
C3 C7 1.474(3) y
C3 C4 1.515(3) ?
C4 C5 1.515(4) ?
C5 C6 1.483(3) y
C1' C7A' 1.507(3) ?
C3' C3A' 1.501(3) ?
C3A' C7A' 1.378(3) ?
C3A' C4' 1.391(3) ?
C4' C5' 1.381(4) ?
C5' C6' 1.381(4) ?
C6' C7' 1.381(4) ?
C7' C7A' 1.383(3) ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 9.4(3) ?
C1' C1 C2 C3 135.9(2) ?
C3' C1 C2 C3 -107.8(2) ?
C6 C1 C2 C8 -173.6(2) ?
C1' C1 C2 C8 -47.1(3) ?
C3' C1 C2 C8 69.1(2) ?
C8 C2 C3 C7 -0.8(4) ?
C1 C2 C3 C7 175.8(2) y
C8 C2 C3 C4 -177.5(2) ?
C1 C2 C3 C4 -0.9(4) ?
C2 C3 C4 C5 21.5(3) ?
C7 C3 C4 C5 -155.5(2) y
C3 C4 C5 C6 -49.8(2) ?
C4 C5 C6 O1 -118.9(2) y
C4 C5 C6 C1 61.5(2) ?
C2 C1 C6 O1 140.0(3) y
C1' C1 C6 O1 13.0(3) ?
C3' C1 C6 O1 -101.2(3) ?
C2 C1 C6 C5 -40.5(3) ?
C1' C1 C6 C5 -167.4(2) ?
C3' C1 C6 C5 78.3(2) ?
C2 C3 C7 O2 19.7(4) y
C4 C3 C7 O2 -163.3(3) y
C2 C3 C7 O3 -160.7(3) y
C4 C3 C7 O3 16.3(4) y
C6 C1 C1' C7A' -121.9(2) ?
C2 C1 C1' C7A' 111.4(2) ?
C3' C1 C1' C7A' -7.0(2) ?
C6 C1 C3' C3A' 126.6(2) ?
C2 C1 C3' C3A' -112.6(2) ?
C1' C1 C3' C3A' 8.1(2) ?
C1 C3' C3A' C7A' -6.6(3) ?
C1 C3' C3A' C4' 174.1(2) ?
C7A' C3A' C4' C5' -0.2(4) ?
C3' C3A' C4' C5' 179.0(2) ?
C3A' C4' C5' C6' -1.1(4) ?
C4' C5' C6' C7' 1.3(4) ?
C5' C6' C7' C7A' -0.2(4) ?
C4' C3A' C7A' C7' 1.3(4) ?
C3' C3A' C7A' C7' -178.1(2) ?
C4' C3A' C7A' C1' -178.5(2) ?
C3' C3A' C7A' C1' 2.2(3) ?
C6' C7' C7A' C3A' -1.1(4) ?
C6' C7' C7A' C1' 178.6(3) ?
C1 C1' C7A' C3A' 3.3(3) ?
C1 C1' C7A' C7' -176.4(3) ?